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I found myself in Imola in January 2016 for a 10-day training at a large industrial conglomerate. Despite being part of the Metropolitan City of Bologna, Imola itself is not nearly as well known, and this mostly as the location of the San Marino Formula One Grand Prix (particularly the infamous 1994 edition, which saw the death of drivers Ayrton Senna and Roland Ratzenberger) until its discontinuation in 2006. After the racing track went silent, Imola went back to being a sleepy town with a sprawling industrial area to the north, but also a well conserved old center with a good deal of things to see, owing to its long history under the rule of various powerful families:

Imola map by Wasso H., on Flickr

Since I was staying in a bland residential suburb to the southeast, and spending my days at the company’s headquarters in the industrial area, the only thing I saw of the town during most of my stay was the view from my room over the surrounding blocks, with the cathedral being faintly visible on the horizon:

Map: 1

View over Imola from my hotel room by Wasso H., on Flickr

View over Imola from my hotel room by Wasso H., on Flickr

And this typically Italian fountain of cast iron, a short distance from the hotel:

Fountain close to my hotel by Wasso H., on Flickr
 

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Discussion Starter #2 (Edited)
It was only after the end of my training that I set off to explore the town’s historical center, starting from the train station where an employee of the company dropped me off. My itinerary will be referenced by the numbers shown on the detailed map below:

Imola itinerary map by Wasso H., on Flickr

Map: 2

Taking Viale Andrea Costa that goes towards the center, one passes next to this interesting villa with the lush garden:

Villa on Viale Andrea Costa by Wasso H., on Flickr

And some bizarrely shaped trees close to it:

Bizarre tree on Viale Andrea Costa by Wasso H., on Flickr

Bizarre tree on Viale Andrea Costa by Wasso H., on Flickr
 

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Map: 5

Arriving to Piazza Medaglie d’Oro (“Square of the Golden Medals”), the visitors encounters these twin red buildings that welcome them to the historic center like a kind of modern gate:

Modern "gate" on Piazza Medaglie d'Oro by Wasso H., on Flickr

Map: 6

A real historic gate however still stands a little further on Via Appia: the Bastioni di Porta Appia (“Appia Gate Bastions”), part of the fortifications that were torn down in the 18th century to make room for the town’s expansion. The lateral towers are all that remains today of the 15th century gate. They were originally joined by a central arch, while a drawbridge opened onto the square in front of them:

Porta Appia gate by Wasso H., on Flickr

Porta Appia gate by Wasso H., on Flickr
 

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Map: 7

Walking further on the historic Via Appia, one passes next to the impressive brick façade of Palazzo Ginnasi, to which we will get back later:

Via Appia by Wasso H., on Flickr

Map: 8

Right afterwards is Palazzo Vacchi, a 19th century neoclassical building by architect Cesare Costa:

Palazzo Vacchi by Wasso H., on Flickr

Its façade is decorated with marble pilasters, busts, and lunettes with bas-relief representations of agriculture, hunting and fishing:

Palazzo Vacchi by Wasso H., on Flickr
 

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Map: 9

Via Appia extends further until Piazzetta dell’Orologgio (“Little Square of the Clock”), situated right in the centre of the pedestrian zone, at the intersection of Via Appia and Via Emilia:

Via Appia by Wasso H., on Flickr

Map: 10

The clock tower standing there is a constant reference point for the people of Imola, with the vault beneath it considered to be the very heart of the town. The clock itself is a 19th century mechanism, and a gift to the Imolese from a French officer in the army of Napoleon, who fell in love with the town and decided to settle there:

Piazzetta dell’Orologgio and the clock tower by Wasso H., on Flickr
 

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Thanks for the pictures.
Anyway saying that Imola is part of the metropolitan area of Bologna it's a bit of a stretch, it is only if we consider the metro area loosely.
The two cities are 33km away and there is almost nothing between them.
I know, I went to Bologna several times when I was there (and will open later a much longer thread for it). The Metropolitan City of Bologna is actually an administrative entity extending much further than the contiguous urban area of Bologna. All public services in Imola state under their name "Imola: Metropolitan City of Bologna", and some of them, like the courthouse, are considered branches of the corresponding central ones based in Bologna, that's why I referenced this denomination in my first post.
 

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I know, I went to Bologna several times when I was there (and will open later a much longer thread for it). The Metropolitan City of Bologna is actually an administrative entity extending much further than the contiguous urban area of Bologna. All public services in Imola state under their name "Imola: Metropolitan City of Bologna", and some of them, like the courthouse, are considered branches of the corresponding central ones based in Bologna, that's why I referenced this denomination in my first post.
The institutional "metropolitan cities" in Italy don't make any sense except for the Cagliari one.

Most of them are just a renamed province, others lacks part of the urban area!
 

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From here I take Via Emilia, Imola’s most central street, which runs in a southeast-northwest direction perpendicularly to Via Appia. The street bears the name of the historical Via Aemilia, built by the Romans to connect Rimini to Piacenza. A series of urban centers appeared along its path in subsequent times, mostly at its correspondence with transversal river valleys, one of which was Forum Cornelii, today’s Imola. The Via Emilia soon became the main element around which the urban, social and economic development of the region was organized, thus giving it its name.

Map: 11

One of the first noticeable buildings I encounter on Via Emilia is this large red one, facing the Nuovo Centro Cittadino on the left (“New Urban Center”), a complex built in the late 1930s and consisting of an imposing brick building and a gallery.

Interesting building on Via Emilia, facing Nuovo Centro Cittadino by Wasso H., on Flickr

Map: 12

A little further stands this other gem, housing the historical Farmacia dell’Ospedale (“Hospital’s Pharmacy”). Inaugurated in 1776, it has remained intact in both the furnishings and the decorations, with its carved wooden shelves still bearing the original 457 majolica vases manufactured in Imola that carry the name of the medicament contained inside. The facade was the only part of the building redesigned in 1928:

Farmacia dell'Ospedale by Wasso H., on Flickr
 

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Map: 14

Right across the street is the imposing brick façade of Palazzo Sassatelli / Monsignani, completed in its current appearance after 1522. The palace was not only the seat of the Sassatelli family, but also housed their private militias:

Palazzo Sassatelli / Monsignani by Wasso H., on Flickr

Map: 15

The main entrance on Via Emilia leads to a courtyard, surrounded by a portico with sandstone columns whose capitals bear the coat of arms of Giovanni Sassatelli, head of the Guelph faction of Imola (the faction supporting the Pope against the Holy Roman emperor). Part of the massive cathedral of Imola can be seen in the back:

Courtyard of Palazzo Sassatelli / Monsignani, with the Duomo of Imola visible in the back by Wasso H., on Flickr
 

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Map: 17

A little further, I encounter one of the city’s most important structures, the former San Francesco complex, built between 1360 and 1380 by Franciscan friars. Originally consisting of two churches and a large adjoining cloister, it was transformed through various works of expansion and reconstruction in the mid 18th century. Then, at the end of the 18th century, the complex’s library acquired the contents of the libraries of all other religious orders, which were confiscated by the government as part of the Napoleonic suppression of convents, eventually becoming a permanent municipal library (Bibilioteca Communale) in 1811. Enriched furthermore throughout the 19th and 20th centuries by the legacies of private citizens who donated valuable collections, it houses nowadays about 450,000 volumes, of which 80,000 are ancient.

San Francesco complex - Municipal library by Wasso H., on Flickr

The kids’ section of the Biblioteca Communale is also located next to the San Francesco complex, in an elegant 18th century building donated to the city in 1965 by the Piani family.

Casa Piani, housing the kids section of the Municipal Library by Wasso H., on Flickr

Map: 18

On the other side is the former upper church of the complex, which was closed during the Napoleonic dominion and transformed into a theater in 1812, a function it still maintains today. The theater closed for security reasons in 1931, to reopen only in 1974 more than forty years later, and was renamed after Ebe Stignani, a Neapolitan opera singer who retired in Imola.

San Francesco complex - Ebe Stignani theater by Wasso H., on Flickr
 

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Map: 20

In the same spot we find the elegant Casa Rambaldi, built in the 14th century and renovated in the 15th century. Only the decorations in the upper part of the façade remain of the original structure. The house belonged to the family of Benvenuto Rambaldi (Benvenuto da Imola), a scholar and historian known for his commentary on Dante's Divine Comedy.

Casa Rambaldi by Wasso H., on Flickr

Map: 20

Across the street stands the Palazzo Miti / Zagnoni / Raffi, which is the final result of the unification and subsequent restoration in the 18th century of three minor buildings dating back to the 15th century. Its composed name comes from the various families who owned the property throughout the centuries. Some Renaissance architectural elements can still be seen on the ground floor, such as the small portico with sandstone columns.

Palazzo Miti / Zagnoni / Raffi by Wasso H., on Flickr

The most important artistic elements however were the result of 17th century additions, especially the monumental chimneys and the frescoes adorning three rooms on the upper floor, with baroque scenes of mythological subjects celebrating the fortune of the Miti family (unfortunately not depicted here, as I hadn’t asked to visit the building)
 

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A little further, I enter a large vaulted gallery perpendicular to the main street, which I learn later is the main entrance to Palazzo Machirelli / dal Pozzo. The palace was built at the end of the 15th century for Michele Machirelli, chancellor of Girolamo Riario (the lord of Imola from 1473 until his assassination in 1488); its simplistic façade was the reason I hadn’t taken a picture of it from the outside. The gallery leads to a courtyard, which is the only surviving part from the period of original construction (the rest having been rebuilt in the 18th century), surrounded by a portico with columns of sandstone and Corinthian capitals, and decorated with terracotta medallions with heads in relief:

Courtyard of Palazzo Machirelli / dal Pozzo by Wasso H., on Flickr

Courtyard of Palazzo Machirelli / dal Pozzo by Wasso H., on Flickr

Map: 22

Across Via Emilia is another vaulted gallery, which is the main entrance to Palazzo dal Monte Casoni. I don’t find the courtyard to which it leads particularly impressive, but take nonetheless a picture of the entrance itself:

Entrance to Palazzo dal Monte Casoni by Wasso H., on Flickr
 

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Map: 23

Next to Palazzo dal Monte Casoni is another church, San Giacomo Maggiore del Carmine (“St James the Greater of the Carmelites”). Together with the adjoining convent, it is linked to the history of the Carmelite Order, present in this place as early as 1300. In the 17th century, impressive works changed the complex to make it take on neoclassical connotations; the façade of the church incorporated the preexisting portico:

San Giacomo Maggiore del Carmine church by Wasso H., on Flickr

Map: 24

San Giacomo Maggiore del Carmine bell tower by Wasso H., on Flickr

Inside the church, the high altar and the choir are worth mentioning, as well as two organs enclosed in decorated 18th century wooden cases:

Map: 23

San Giacomo Maggiore del Carmine church by Wasso H., on Flickr

San Giacomo Maggiore del Carmine church by Wasso H., on Flickr
 
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